If you’re a fan of the quirky, heartfelt romantic comedy-drama 500 Days of Summer, chances are you fell in love with the offbeat storytelling, relatable characters, and bittersweet exploration of modern relationships. Starring Joseph Gordon-Levitt and Zooey Deschanel, this indie gem struck a chord with audiences looking for a more realistic take on love and dating.
So if you adored 500 Days of Summer and are craving more movies in the same vein, look no further! I’ve compiled a list of 15 films that capture a similar spirit and tone. Get ready for some laughter, tears, and plenty of introspection as we dive into these must-watch movies for any 500 Days of Summer fan.
1. Eternal Sunshine of the Spotless Mind (2004)
Topping the list is Eternal Sunshine of the Spotless Mind, a mind-bending sci-fi romantic drama starring Jim Carrey and Kate Winslet. The film follows a couple who erase each other from their memories after a painful breakup, only to find themselves inexplicably drawn to each other again.
Like 500 Days of Summer, this movie plays with the traditional romantic comedy structure, jumping around in time and delving into the complexities of relationships. It’s a poignant, thought-provoking exploration of love, loss, and the power of memory. If you enjoyed the non-linear storytelling and emotional depth of 500 Days of Summer, Eternal Sunshine of the Spotless Mind is a must-see.
2. Annie Hall (1977)
Considered one of the greatest romantic comedies of all time, Annie Hall stars Woody Allen and Diane Keaton as a neurotic comedian and an aspiring singer navigating the ups and downs of their relationship. Much like 500 Days of Summer, the film is told largely from the male protagonist’s point of view as he tries to make sense of love and life.
With its witty dialogue, fourth wall-breaking moments, and bittersweet ending, Annie Hall set the template for many modern romantic comedies, including 500 Days of Summer. It’s a classic that still feels fresh and relevant decades later.
3. Garden State (2004)
Garden State, written and directed by Zach Braff, follows a struggling actor who returns to his hometown for his mother’s funeral and falls for a quirky local girl, played by Natalie Portman. Like 500 Days of Summer, it’s a coming-of-age story that deals with themes of love, loss, and self-discovery.
With its indie sensibility, memorable soundtrack, and offbeat humor, Garden State captures the uncertainty and ennui of young adulthood in a way that will resonate with fans of 500 Days of Summer. It’s a touching, quietly profound film that stays with you long after the credits roll.
4. The Perks of Being a Wallflower (2012)
Based on the beloved novel by Stephen Chbosky, The Perks of Being a Wallflower follows a shy, introverted high school freshman (Logan Lerman) as he navigates first love, friendship, and mental health issues with the help of two charismatic seniors (Emma Watson and Ezra Miller).
Like 500 Days of Summer, the film doesn’t shy away from the darker aspects of growing up and falling in love. It’s a poignant, emotionally honest coming-of-age story that captures both the joy and pain of adolescence. With its stellar cast and sensitive handling of heavy topics, The Perks of Being a Wallflower is a modern classic that will speak to anyone who’s ever felt like an outsider.
5. Juno (2007)
Juno, written by Diablo Cody and directed by Jason Reitman, tells the story of a quick-witted teenage girl (Ellen Page) who finds herself unexpectedly pregnant and decides to give her baby up for adoption to a wealthy couple (Jennifer Garner and Jason Bateman). Along the way, she navigates her relationships with her best friend and co-parent (Michael Cera), her supportive father (J.K. Simmons), and her sarcastic but caring stepmother (Allison Janney).
Like 500 Days of Summer, Juno tackles heavy themes with humor and heart. It’s a smart, funny, and ultimately moving film that doesn’t condescend to its teenage characters or its audience. With its sharp dialogue, memorable characters, and killer soundtrack, Juno is a modern classic that still feels fresh and relevant today.
6. Celeste and Jesse Forever (2012)
Celeste and Jesse Forever stars Rashida Jones and Andy Samberg as a divorced couple trying to maintain their friendship while pursuing new relationships. Like 500 Days of Summer, it’s a romantic comedy that subverts the genre’s conventions, exploring the messy, complicated nature of love and friendship in the modern world.
With its witty dialogue, likable characters, and bittersweet tone, Celeste and Jesse Forever is a charming, relatable film that will resonate with anyone who’s ever struggled to let go of a past relationship. Jones and Samberg have great chemistry, and the supporting cast (including Elijah Wood, Emma Roberts, and Ari Graynor) is equally strong.
7. Ruby Sparks (2012)
Ruby Sparks, written by Zoe Kazan and directed by Jonathan Dayton and Valerie Faris (the team behind Little Miss Sunshine), follows a struggling novelist (Paul Dano) who writes his dream girl into existence, only to find that their relationship is more complicated than he imagined.
Like 500 Days of Summer, Ruby Sparks is a clever, meta-fictional take on the romantic comedy genre that explores the gap between fantasy and reality. It’s a funny, poignant, and ultimately thought-provoking film that asks big questions about love, creativity, and control. Kazan and Dano (a real-life couple) have great chemistry, and the supporting cast (including Chris Messina, Annette Bening, and Antonio Banderas) is equally strong.
8. Beginners (2010)
Beginners, written and directed by Mike Mills, tells the story of a young man (Ewan McGregor) coming to terms with his father’s death and late-in-life coming out, while also falling for a charming French actress (Mélanie Laurent). Like 500 Days of Summer, it’s a poignant, bittersweet exploration of love, loss, and self-discovery.
With its non-linear structure, quirky humor, and deeply felt emotions, Beginners is a unique and moving film that will stay with you long after the credits roll. McGregor and Laurent have great chemistry, and Christopher Plummer (who won an Oscar for his performance) is unforgettable as the father embracing his true self in his final years.
9. Obvious Child (2014)
Obvious Child stars Jenny Slate as a struggling comedian who finds herself unexpectedly pregnant after a one-night stand and decides to have an abortion. Like 500 Days of Summer, it’s a romantic comedy that tackles heavy themes with humor and heart, never shying away from the messy realities of life and love.
With its sharp dialogue, likable characters, and refreshingly honest approach to a taboo subject, Obvious Child is a funny, moving, and ultimately empowering film that will resonate with anyone who’s ever faced a difficult decision. Slate is a revelation in the lead role, and the supporting cast (including Jake Lacy, Gaby Hoffmann, and David Cross) is equally strong.
10. Seeking a Friend for the End of the World (2012)
Seeking a Friend for the End of the World stars Steve Carell and Keira Knightley as two strangers who embark on a road trip together as an asteroid hurtles towards Earth, threatening to destroy all life on the planet. Like 500 Days of Summer, it’s a romantic comedy with a twist, exploring love and connection in the face of impending doom.
With its offbeat humor, poignant moments, and unexpected twists, Seeking a Friend for the End of the World is a unique and moving film that will make you laugh, cry, and ponder the meaning of life. Carell and Knightley have great chemistry, and the supporting cast (including Adam Brody, Patton Oswalt, and Melanie Lynskey) is equally strong.
11. The Spectacular Now (2013)
The Spectacular Now, based on the novel by Tim Tharp, follows a charming but aimless high school senior (Miles Teller) who falls for a shy, introverted classmate (Shailene Woodley) and starts to reevaluate his life choices. Like 500 Days of Summer, it’s a coming-of-age story that deals with themes of love, identity, and the search for meaning in a confusing world.
With its naturalistic performances, poignant moments, and honest portrayal of teenage life, The Spectacular Now is a quietly powerful film that will resonate with anyone who’s ever struggled to find their place in the world. Teller and Woodley have incredible chemistry, and the supporting cast (including Brie Larson, Jennifer Jason Leigh, and Kyle Chandler) is equally strong.
12. Stuck in Love (2012)
Stuck in Love follows a family of writers – a divorced father (Greg Kinnear), his teenage children (Lily Collins and Nat Wolff), and his ex-wife (Jennifer Connelly) – as they navigate love, heartbreak, and the challenges of the creative life. Like 500 Days of Summer, it’s a poignant, bittersweet exploration of relationships and the power of storytelling.
With its talented ensemble cast, sharp dialogue, and emotionally resonant moments, Stuck in Love is a charming and insightful film that will appeal to anyone who’s ever loved and lost. Kinnear, Connelly, Collins, and Wolff all give strong performances, and the supporting cast (including Logan Lerman, Kristen Bell, and Stephen King in a cameo role) is equally impressive.
13. The Five-Year Engagement (2012)
The Five-Year Engagement stars Jason Segel and Emily Blunt as a couple whose relationship is tested by a series of setbacks and delays on their way to the altar. Like 500 Days of Summer, it’s a romantic comedy that’s not afraid to explore the darker, more complicated aspects of love and commitment.
With its clever script, likable characters, and perfect balance of humor and heart, The Five-Year Engagement is a refreshingly honest and relatable film that will resonate with anyone who’s ever been in a long-term relationship. Segel and Blunt have great chemistry, and the supporting cast (including Chris Pratt, Alison Brie, and Rhys Ifans) is equally strong.
14. Definitely, Maybe (2008)
Definitely, Maybe stars Ryan Reynolds as a soon-to-be-divorced father who tells his young daughter (Abigail Breslin) the story of his past relationships, changing the names so she has to guess which one became her mother. Like 500 Days of Summer, it’s a romantic comedy with a unique structure and a poignant exploration of love and fate.
With its charming performances, clever script, and heartfelt moments, Definitely, Maybe is a sweet and satisfying film that will leave you with a smile on your face. Reynolds is perfectly cast as the likable but commitment-phobic protagonist, and the supporting cast (including Isla Fisher, Elizabeth Banks, and Rachel Weisz) is equally strong.
15. Crazy, Stupid, Love (2011)
Last but not least, Crazy, Stupid, Love follows a recently divorced man (Steve Carell) who seeks the help of a smooth-talking player (Ryan Gosling) to rediscover his manhood and win back his wife (Julianne Moore). Like 500 Days of Summer, it’s a romantic comedy that’s not afraid to explore the messier, more complicated aspects of love and relationships.
With its all-star cast, sharp dialogue, and perfect balance of humor and heart, Crazy, Stupid, Love is a smart, funny, and ultimately moving film that will resonate with anyone who’s ever been in love. Carell, Gosling, Moore, and Emma Stone (as Carell’s daughter) all give fantastic performances, and the supporting cast (including Marisa Tomei and Kevin Bacon) is equally strong.
So there you have it – 15 movies like 500 Days of Summer that will give you all the feels. Whether you’re in the mood for a quirky indie romance, a poignant coming-of-age story, or a clever subversion of the romantic comedy genre, these films have something for everyone. So grab some popcorn, settle in, and get ready to laugh, cry, and fall in love all over again.
